We Welcome Your Application to Join Us!

We build each of our groups with care, keeping the groups small (no more than twelve students), and paying close attention to age, grade, gender, and the mix of hometowns and schools. Our goal is to put together great groups — groups where nice kids thrive in a supportive, wholesome, and caring environment. Please note: availability as shown is based on students traveling without a friend; if your child is interested in traveling with a friend, please call our office for availability.

Important Information about Availability


This departure of this trip has good availability. Apply as soon as possible since availability changes quickly.


This departure of this trip has limited availability. Apply as soon as possible, and on receipt of your application, if space is still available, we’ll confirm a spot for you. If all of the spots are taken, we’ll call you to discuss options.


This departure of this trip is currently full — please call us to discuss options.

How to Apply

Apply online using a credit card for the $795 deposit (your card will not be charged until we confirm a spot for you). Applications are reviewed in the order in which they are received (we do not hold spots over the phone).

When to Apply

The flow of applications starts in July and peaks in January/February. Some groups fill by the December holidays, and others will have space into the late spring. Our advice? Apply as soon as possible — it only takes a few minutes — and we’ll get to work right away to find a great spot for you.


Call (413.458.9672) or email (info@overlandsummers.com). We look forward to hearing from you.


Meg Pritchard

Assistant Director, Trip Planning

Email Meg

As a child, I was always returning home with grass stains and muddy shoes.

Growing up in central Virginia, I spent most of my time playing in the woods beside my house. Whether hiking trails, skipping stones, or dodging trees while sledding, I was happiest when I was exploring the world around me. These long afternoons outside with friends and family made me love sharing the outdoors with others.

While leading outdoor orientation trips for first-year students at Yale, I found my relationships with students and other leaders to be incredibly rewarding. Knowing that I was looking for other, similar opportunities, our orientation director recommended Overland. In 2018, I led Alaska Expedition and was amazed by the kindness and tenacity of my students. I returned in 2019 to lead High Sierra Expedition with students who actively sought to bring out the best in each other. More than anything, it is the people who make Overland such a rewarding and enriching community.

From my first day in Williamstown, it has been clear that the year-round staff is a team. From group hikes in the Berkshires to morning coffee breaks, we support each other in and out of the office. It is a privilege to work with driven, dedicated coworkers to create incredible trips for our community of students.